Acrylonitrile
| |||
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Prop-2-enenitrile | |||
Other names | |||
Identifiers | |||
3D model (
JSmol ) |
|||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
|
100.003.152 | ||
EC Number |
| ||
KEGG | |||
PubChem CID
|
|||
RTECS number
|
| ||
UNII | |||
UN number | 1093 | ||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
Properties | |||
C3H3N | |||
Molar mass | 53.064 g·mol−1 | ||
Appearance | Colourless liquid | ||
Density | 0.81 g/cm3 | ||
Melting point | −84 °C (−119 °F; 189 K) | ||
Boiling point | 77 °C (171 °F; 350 K) | ||
70 g/L | |||
log P | 0.19[2] | ||
Vapor pressure | 83 mmHg[1] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
|
|||
NFPA 704 (fire diamond) | |||
Flash point | −1 °C; 30 °F; 272 K | ||
471 °C (880 °F; 744 K) | |||
Explosive limits
|
3–17% | ||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
|
500 ppm (rat, 4 h) 313 ppm (mouse, 4 h) 425 ppm (rat, 4 h)[3] | ||
LCLo (lowest published)
|
260 ppm (rabbit, 4 h) 575 ppm (guinea pig, 4 h) 636 ppm (rat, 4 h) 452 ppm (human, 1 h)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
TWA 2 ppm C 10 ppm [15-minute] [skin][1] | ||
REL (Recommended)
|
Ca TWA 1 ppm C 10 ppm [15-minute] [skin][1] | ||
IDLH (Immediate danger) |
85 ppm[1] | ||
Safety data sheet (SDS) | ICSC 0092 | ||
Related compounds | |||
Related nitriles
|
acetonitrile propionitrile | ||
Related compounds
|
acrylic acid acrolein | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Acrylonitrile is an
Acrylonitrile is one of the components of
Structure and basic properties
Acrylonitrile is an
Production
Acrylonitrile was first synthesized by the French chemist Charles Moureu in 1893.[7] Acrylonitrile is produced by
- 2 CH3−CH=CH2 + 2 NH3 + 3 O2 → 2 CH2=CH−C≡N + 6 H2O
In the SOHIO process,
Alternative routes
Various
Uses
Acrylonitrile is used principally as a
- 2 CH2=CHCN + 2 e− + 2 H+ → NCCH2−CH2−CH2−CH2CN
Acrylonitrile is also a precursor in the manufacture of acrylamide and acrylic acid.[5]
Synthesis of chemicals
Hydrogenation of acrylonitrile is one route to propionitrile. Hydrolysis with sulfuric acid gives acrylamide sulfate, CH=CHC(O)NH2·H2SO4. This salt can be converted to acrylamide with treatment with base or to methyl acrylate by treatment with methanol.[5]
The reaction of acrylonitrile with protic nucleophiles is a common route to a variety of specialty chemicals. The process is called cyanoethylation:
- YH + H2C=CHCN → Y−CH2−CH2CN
Typical protic nucleophiles are alcohols, thiols, and especially amines.[17]
Acrylonitrile and derivatives, such as 2-chloroacrylonitrile, are
Health effects
Acrylonitrile is moderately
It evaporates quickly at room temperature (20 °C) to reach dangerous concentrations;
There are two main excretion processes of acrylonitrile. The primary method is excretion in urine when acrylonitrile is metabolized by being directly conjugated to glutathione. The other method is when acrylonitrile is enzymatically converted into 2-cyanoethylene oxide which will produce cyanide end products that ultimately form thiocyanate, which is excreted via urine.[25] Exposure can thus be detected via blood draws and urine sampling.[18]
Incidents
A large amount of acrylonitrile (approximately 6500 tons) leaked from an industrial polymer plant owned by Aksa Akrilik after the violent 17 August earthquake in Turkey. Over 5000 people were affected and the exposed animals had died.[26] The leak was only noticed by the company 8 hours after the incident. Healthcare workers did not know about the health effects of acrylonitrile and tried to treat the victims with painkillers and IV fluids.[27] One lawyer, Ayşe Akdemir, sued the company with 44 families as the plaintiffs.[27] Aksa Akrilik was sued by 200 residents who were affected by acrylonitrile.[28] An increase in cancer cases in the area was confirmed by the Turkish Medical Association,[28] as the cancer rate in the affected area has increased by 80%, from 1999 to April 2002.[27] In 2003, the owner of Aksa Akrilik has died from lung cancer related to acrylonitrile exposure.[27] As of 2001, this is the largest acrylonitrile leak known.[26]
Occurrence
Acrylonitrile is not naturally formed on Earth. It has been detected at the sub-ppm level at industrial sites. It persists in the air for up to a week. It decomposes by reacting with oxygen and hydroxyl radical to form formyl cyanide and formaldehyde.[29] Acrylonitrile is harmful to aquatic life.[24] Acrylonitrile has been detected in the atmosphere of Titan, a moon of Saturn.[30][31][32] Computer simulations suggest that on Titan conditions exist such that the compound could form structures similar to cell membranes and vesicles on Earth, called azotosomes.[30][31]
References
- ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0014". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Acrylonitrile_msds".
- ^ a b "Acrylonitrile". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Medical Management Guidelines for Acrylonitrile". Agency for Toxic Substances & Disease Registry. Retrieved 2020-06-10.
- ^ ISBN 978-3527306732.
- ISBN 978-0-8155-1551-7, retrieved 2023-11-20
- ^
- Moureu, C. (1893). "Contribution à l'étude de l'acide acrylique et de ses dérivés" [Contribution to the study of acrylic acid and of its derivatives]. Annales de chimie et de physique. 7th. 2: 145–212. See especially pp. 187–189 ("Nitrile acrylique ou cyanure de vinyle (Propène-nitrile)").
- Moureu, C. (1893). "Nitrile acrylique, cyanure de vinyle (propène-nitrile)" [Acrylic nitrile, vinyl cyanide (propenenitrile)]. Bulletin de la Société Chimique de France. 3rd. 9: 424–427.
- ^ "The Sohio Acrylonitrile Process". American Chemical Society National Historic Chemical Landmarks. Archived from the original on 2013-02-23. Retrieved 2013-05-13.
- ^ .
- .
- .
- ^ S2CID 99550463.
- ^ ISSN 0920-5861.
- ISSN 1463-9262.
- ^ Ellis, Paul G (1972). A radiation-chemical study of the hydrodimerisation of acrylonitrile. UK: Leeds University, Ph D thesis.
- .
- ISBN 978-3527306732.
- ^ a b "Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide". IARC Monographs, Volume 71 (1999)
- ^ Acrylonitrile Fact Sheet (CAS No. 107-13-1). epa.gov
- PMID 21802474
- ^ Pu X, Kamendulis LM, Klaunig JE. Acrylonitrile-induced oxidative stress and oxidative DNA damage in male Sprague-Dawley rats. Toxicol Sci. 2009;111(1):64-71. doi:10.1093/toxsci/kfp133
- ^ "Acrylonitrile: Carcinogenic Potency Database".
- PMID 24248151.
- ^ a b c "CDC – Acrylonitrile – International Chemical Safety Cards". www.cdc.gov. NIOSH. Retrieved 2015-07-31.
- ^ a b Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1). epa.gov
- ^ a b Nadi Bakırcı (2001). "ENDÜSTRİYEL BİR ÇEVRE FELAKETİ: AKRİLONİTRİL" [AN INDUSTRIAL ENVIRONMENT DISASTER: ACRYLONITRILE]. Turkish Medical Association.
- ^ a b c d Fatma Dalokay (30 November 2020). "17 Ağustos 1999 Depremi: Akrilonitril Zehirlenmesi" [17 August 1999 Earthquake: Acrylonitrile Poisoning]. Tabella.
- ^ a b "İSO'nun şaşırtan çevre ödülü Aksa'nın". Hürriyet. 26 June 2005.
- .
- ^ a b Wall, Mike (28 July 2017). "Saturn Moon Titan Has Molecules That Could Help Make Cell Membranes". Space.com. Retrieved 29 July 2017.
- ^ PMID 28782019.
- ^ Kaplan, Sarah (8 August 2017). "This weird moon of Saturn has some essential ingredients for life". The Washington Post. Retrieved 8 August 2017.
External links
- National Pollutant Inventory – Acrylonitrile
- Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens Archived 2012-09-03 at the Wayback Machine
- Acrylonitrile – Integrated Risk Information System, U.S. Environmental Protection Agency
- CDC – NIOSH Pocket Guide to Chemical Hazards – Acrylonitrile
- OSHA Table Z-1 for Air Contaminants